Synthesis of tetrasubstituted and functionalized enol ethers by E-selective olefination of esters with ynolates

被引:36
作者
Shindo, M [1 ]
Kita, T [1 ]
Kumagai, T [1 ]
Matsumoto, K [1 ]
Shishido, K [1 ]
机构
[1] Univ Tokushima, Inst Hlth Biosci, Grad Sch, Tokushima 7708505, Japan
关键词
D O I
10.1021/ja0561082
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
We have developed the E-selective olefination of ester carbonyls to afford tetrasubstituted, functionalized olefins and the C-S insertion of thiol esters to give β-keto thiol esters via ynolates. Copyright © 2006 American Chemical Society.
引用
收藏
页码:1062 / 1063
页数:2
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共 37 条
[1]  
Davis B.R., 1991, COMPREHENSIVE ORGANI, V2, P795
[2]   Electronic control of stereoselectivities of electrocyclic reactions of cyclobutenes: A triumph of theory in the prediction of organic reactions [J].
Dolbier, WR ;
Koroniak, H ;
Houk, KN ;
Sheu, CM .
ACCOUNTS OF CHEMICAL RESEARCH, 1996, 29 (10) :471-477
[3]   POLYMER SYNTHESIS AND ORGANOTRANSITION METAL CHEMISTRY [J].
GRUBBS, RH ;
TUMAS, W .
SCIENCE, 1989, 243 (4893) :907-915
[4]   New carbonyl olefination using thioacetals [J].
Horikawa, Y ;
Watanabe, M ;
Fujiwara, T ;
Takeda, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (05) :1127-1128
[5]   STEREOSELECTIVE SUBSTITUENT EFFECTS ON CONROTATORY ELECTROCYCLIC REACTIONS OF CYCLOBUTENES [J].
KIRMSE, W ;
RONDAN, NG ;
HOUK, KN .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (25) :7989-7991
[6]   NEW COUPLING REAGENTS IN PEPTIDE CHEMISTRY [J].
KNORR, R ;
TRZECIAK, A ;
BANNWARTH, W ;
GILLESSEN, D .
TETRAHEDRON LETTERS, 1989, 30 (15) :1927-1930
[7]   Methylenation of esters with bis(iodozincio)methane-TiCl2-TMEDA system [J].
Matsubara, S ;
Ukai, K ;
Mizuno, T ;
Utimoto, K .
CHEMISTRY LETTERS, 1999, (08) :825-826
[8]   Hyperconjugative effects in the stereoselective ring-opening reactions of oxetenoxides [J].
Mori, S ;
Shindo, M .
ORGANIC LETTERS, 2004, 6 (22) :3945-3948
[9]  
OKAZOE T, 1987, J ORG CHEM, V52, P4412
[10]   TITANIUM-MEDIATED CARBONYL OLEFINATIONS .2. BENZYLIDENATIONS OF CARBONYL-COMPOUNDS WITH DIBENZYLTITANOCENE [J].
PETASIS, NA ;
BZOWEJ, EI .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (05) :1327-1330